4.5 Article

Nickel-Catalyzed C-F/N-H Annulation of 2-(2-Fluoroaryl) N-Heteroaromatic Compounds with Alkynes: Activation of C-F Bonds

Journal

SYNTHESIS-STUTTGART
Volume 53, Issue 17, Pages 3075-3080

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1337-5504

Keywords

C-F bond activation; nickel; alkyne; annulation; N-heteroaromatic compounds

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) [17H06091]

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The reaction involves annulation of 2-(2-fluoroaryl) N-heteroaromatic compounds with internal alkynes in the presence of a catalytic amount of a nickel complex. It shows high functional group compatibility and requires the presence of a strong base, such as KOBut or LiOBut, for the reaction to proceed.
The reaction of 2-(2-fluoroaryl) N-heteroaromatic compounds, such as benzimidazole and indole derivatives, with internal alkynes in the presence of a catalytic amount of a nickel complex results in C-F/N-H annulation with alkynes. The reaction shows a high functional group compatibility. The presence of a strong base, such as KOBut or LiOBut, is required for the reaction to proceed.

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